When you’re vacationing or enjoying a luxury yacht charter on the tranquil Caribbean Sea, imagine that 300 years ago the most notorious gangsters of the seas sailed these same waters, dropping hook in the same coves. Here we reveal six real pirates of the Caribbean that certainly were not the affable swashbuckling miscreants of the Silver Screen. 1. Edward Teach, aka Blackbeard Born in Bristol, England, Teach came to the Caribbean as a privateer. Following the end of Queen Anne’s War, Teach converted a captured warship into a pirate ship he would call Queen Anne’s Revenge and continued his reign of terror along the U.S. eastern seaboard and throughout the Caribbean. Although Blackbeard was considered an extremely brave man, by modern standards he was nothing short of psychotic. In battle, Teach would place lit matches under his hat and in his beard so his enemies would think his head was on fire. If victims would hesitate in handing over jewelry, Blackbeard would simply brandish a cutlass or ax and take the entire appendage. Teach once shot his own first mate so that people would remember his name and just how cruel he could be. During Blackbeard’s reign in the Caribbean, his only adversary was disease. Teach once put the town of Charleston, South Carolina, under siege — holding a prominent citizen hostage — to gain a ransom of medicine to treat himself and a number of his crew for syphilis. In 1718, a military force led by Lt. Robert Maynard was sent to dispatch Blackbeard. The two men came to blows near Ocracoke Island, North Carolina, and legend has it that the hand-to-hand battle lasted 40 minutes. It is said that Maynard stabbed Blackbeard more than 20 times and shot him no less than five times before Blackbeard finally died of blood loss.

When you’re vacationing or enjoying a luxury yacht charter on the tranquil Caribbean Sea, imagine that 300 years ago the most notorious gangsters of the seas sailed these same waters, dropping hook in the same coves.

Here we reveal six real pirates of the Caribbean that certainly were not the affable swashbuckling miscreants of the Silver Screen.

1. Edward Teach, aka Blackbeard

Born in Bristol, England, Teach came to the Caribbean as a privateer. Following the end of Queen Anne’s War, Teach converted a captured warship into a pirate ship he would call Queen Anne’s Revenge and continued his reign of terror along the U.S. eastern seaboard and throughout the Caribbean.

Although Blackbeard was considered an extremely brave man, by modern standards he was nothing short of psychotic. In battle, Teach would place lit matches under his hat and in his beard so his enemies would think his head was on fire. If victims would hesitate in handing over jewelry, Blackbeard would simply brandish a cutlass or ax and take the entire appendage. Teach once shot his own first mate so that people would remember his name and just how cruel he could be. During Blackbeard’s reign in the Caribbean, his only adversary was disease. Teach once put the town of Charleston, South Carolina, under siege — holding a prominent citizen hostage — to gain a ransom of medicine to treat himself and a number of his crew for syphilis.

In 1718, a military force led by Lt. Robert Maynard was sent to dispatch Blackbeard. The two men came to blows near Ocracoke Island, North Carolina, and legend has it that the hand-to-hand battle lasted 40 minutes. It is said that Maynard stabbed Blackbeard more than 20 times and shot him no less than five times before Blackbeard finally died of blood loss.

Nau is widely considered one of the most ruthless and barbaric pirates ever to set sail in the Caribbean. Nau arrived in Martinique from France as an indentured servant child. Following his period of servitude, Nau relocated to Hispaniola where he joined the Buccaneers. Having won favor with the French Governor of Tortuga, Nau was given command of his own ship. Sanctioned by the French government to attack Spanish enemies, he would develop an insatiable blood-thirst and penchant for torture (particularly against the Spanish), which prolonged his reign of terror well into times of peace between France and Spain. As word of Nau’s unspeakable cruelty spread, his successes became fewer. Spanish ships would fight to the death rather than surrender to the merciless Nau. Partnering with freebooter Michel de Basco, Nau was able to amass a fleet of eight ships and 400 men and managed to seize the towns of Gibraltar and Maracaibo in the Gulf of Venezuela, where the townspeople endured unimaginable atrocities. The invading pirates garnered more than 260,000 pieces of eight (aka Spanish dollar), as well as other booty, but these spoils soon vanished into the pockets of Tortuga’s tavern keepers and prostitutes. Desperate for treasure, Nau continued his assaults on Spanish ships and the colonies. With faltering success, his hatred of the Spanish intensified. Fearful of their psychotic captain, Nau’s crew mutinied and left him with a single craft that ran aground off Las Petras Islands. While trying to recruit a new crew, Nau was attacked and captured by local natives. It is said that the Indians tore Nau apart, throwing pieces of his body in a fire and scattering the ashes so no trace of the horrible pirate would remain.

Nau is widely considered one of the most ruthless and barbaric pirates ever to set sail in the Caribbean. Nau arrived in Martinique from France as an indentured servant child. Following his period of servitude, Nau relocated to Hispaniola where he joined the Buccaneers. Having won favor with the French Governor of Tortuga, Nau was given command of his own ship. Sanctioned by the French government to attack Spanish enemies, he would develop an insatiable blood-thirst and penchant for torture (particularly against the Spanish), which prolonged his reign of terror well into times of peace between France and Spain.

As word of Nau’s unspeakable cruelty spread, his successes became fewer. Spanish ships would fight to the death rather than surrender to the merciless Nau. Partnering with freebooter Michel de Basco, Nau was able to amass a fleet of eight ships and 400 men and managed to seize the towns of Gibraltar and Maracaibo in the Gulf of Venezuela, where the townspeople endured unimaginable atrocities. The invading pirates garnered more than 260,000 pieces of eight (aka Spanish dollar), as well as other booty, but these spoils soon vanished into the pockets of Tortuga’s tavern keepers and prostitutes.

Desperate for treasure, Nau continued his assaults on Spanish ships and the colonies. With faltering success, his hatred of the Spanish intensified. Fearful of their psychotic captain, Nau’s crew mutinied and left him with a single craft that ran aground off Las Petras Islands. While trying to recruit a new crew, Nau was attacked and captured by local natives. It is said that the Indians tore Nau apart, throwing pieces of his body in a fire and scattering the ashes so no trace of the horrible pirate would remain.

Jack Rackham was not an especially ruthless pirate nor was he notably successful. What keeps Calico Jack in the forefront among his peers is that two of his crew — and likely the fiercest — were women. Rackham met Anne Bonny, the wife of a smuggler, in The Bahamas. The two fell in love, and when attempts to buy Bonny from her husband failed, Bonny joined Rackham’s crew as a pirate. Rackham and his crew soon captured a ship and gave that crew the option of joining him. Among the new additions was a magnificent swordsman. Over time, Bonny and this new crewman would forge a close relationship. When Rackham’s jealousy drove him into a rage, Bonny divulged that the new sailor was also a woman named Mary Read. History has well documented that Rackham attacked several ships where Bonny and Read fought viciously and openly as women. The pair quickly became legendary throughout the Caribbean. As Rackham’s notoriety started to pale in comparison to his unusual crew, he began to succumb to alcohol. At the time of Rackham’s defeat, an already drunken crew (with the exception of Bonny and Read) panicked when the main mast was shot down. With defeat eminent, the crew dashed belowdecks to finish off the rum, knowing it would be the last they would ever have. It is reported that Rackham was granted a last request to see Bonny before his execution. Still seething, she is quoted as saying, “I’m sorry to see you here, but had you fought like a man, you needn’t hang like a dog.”

Jack Rackham was not an especially ruthless pirate nor was he notably successful. What keeps Calico Jack in the forefront among his peers is that two of his crew — and likely the fiercest — were women. Rackham met Anne Bonny, the wife of a smuggler, in The Bahamas. The two fell in love, and when attempts to buy Bonny from her husband failed, Bonny joined Rackham’s crew as a pirate. Rackham and his crew soon captured a ship and gave that crew the option of joining him. Among the new additions was a magnificent swordsman. Over time, Bonny and this new crewman would forge a close relationship. When Rackham’s jealousy drove him into a rage, Bonny divulged that the new sailor was also a woman named Mary Read.

History has well documented that Rackham attacked several ships where Bonny and Read fought viciously and openly as women. The pair quickly became legendary throughout the Caribbean. As Rackham’s notoriety started to pale in comparison to his unusual crew, he began to succumb to alcohol. At the time of Rackham’s defeat, an already drunken crew (with the exception of Bonny and Read) panicked when the main mast was shot down. With defeat eminent, the crew dashed belowdecks to finish off the rum, knowing it would be the last they would ever have.

It is reported that Rackham was granted a last request to see Bonny before his execution. Still seething, she is quoted as saying, “I’m sorry to see you here, but had you fought like a man, you needn’t hang like a dog.”

Black Bart is often referred to as one of the most successful pirates. He was certainly an incredibly profitable pirate, reportedly taking more than 200 ships and treasure worth tens of millions by today’s standards, but the term “successful” becomes rather debatable as his career lasted only two-and-a-half years before coming to a violent end. Born in southern Wales in the early 1680s, Roberts first appears in the history books as the third mate aboard a British slave ship. In 1719, pirate Howell Davis took the ship and Roberts then became forced labor aboard. Roberts took to pirate life, and when Davis was killed during an attack, Roberts was elected captain. Roberts’ first act as captain was to brutally avenge the death of Davis. Roberts was stylish and vain with a penchant for fine, brightly colored clothing and exquisite jewels. Descriptions of Roberts no doubt have had an impact on how pirates are portrayed in Hollywood. Historical accounts report that Roberts wore scarlet britches, a waist sash and overcoat. A tri-cornered hat was his hallmark as was a diamond-encrusted cross, which he wore on an ostentatious gold chain. As the cross indicates, Roberts was an oddly pious man. He held religious services aboard the ship and never attacked on the Sabbath. He also prohibited the consumption of alcohol on board, as well as gambling and fornication. Those who were loyal to Roberts were fiercely so, but historians believe as much as one-third of his crew were forced pirates. To prevent desertions, Roberts avoided hospitable ports and would often remain at sea for long periods of time. Roberts’ success as a pirate is reported to have brought transatlantic shipping almost to a standstill. In February 1722, Roberts was duped by a British warship under the command of Chaloner Ogle. Raising the French colors, Ogle managed to deceive Roberts, defeat his ship and kill its master in two exchanges. Roberts’ despondent crew weighted his body and cast him overboard fulfilling a promise not to allow him to be captured either in life or death. The trials held for the remainder of his crew are some of the most well-known in British history.

Black Bart is often referred to as one of the most successful pirates. He was certainly an incredibly profitable pirate, reportedly taking more than 200 ships and treasure worth tens of millions by today’s standards, but the term “successful” becomes rather debatable as his career lasted only two-and-a-half years before coming to a violent end.

Born in southern Wales in the early 1680s, Roberts first appears in the history books as the third mate aboard a British slave ship. In 1719, pirate Howell Davis took the ship and Roberts then became forced labor aboard. Roberts took to pirate life, and when Davis was killed during an attack, Roberts was elected captain. Roberts’ first act as captain was to brutally avenge the death of Davis.

Roberts was stylish and vain with a penchant for fine, brightly colored clothing and exquisite jewels. Descriptions of Roberts no doubt have had an impact on how pirates are portrayed in Hollywood. Historical accounts report that Roberts wore scarlet britches, a waist sash and overcoat. A tri-cornered hat was his hallmark as was a diamond-encrusted cross, which he wore on an ostentatious gold chain.

As the cross indicates, Roberts was an oddly pious man. He held religious services aboard the ship and never attacked on the Sabbath. He also prohibited the consumption of alcohol on board, as well as gambling and fornication. Those who were loyal to Roberts were fiercely so, but historians believe as much as one-third of his crew were forced pirates. To prevent desertions, Roberts avoided hospitable ports and would often remain at sea for long periods of time. Roberts’ success as a pirate is reported to have brought transatlantic shipping almost to a standstill.

In February 1722, Roberts was duped by a British warship under the command of Chaloner Ogle. Raising the French colors, Ogle managed to deceive Roberts, defeat his ship and kill its master in two exchanges.

Roberts’ despondent crew weighted his body and cast him overboard fulfilling a promise not to allow him to be captured either in life or death. The trials held for the remainder of his crew are some of the most well-known in British history.

Born to Scottish slaves on the island of Barbados, Greaves became a pirate when, in a desperate attempt to escape, he stowed away on a ship belonging to a notoriously cruel pirate named Captain Hawkins. Although forced to become a pirate, Greaves quickly adapted to the new role. However, life as a slave left him with little tolerance for brutality, and when the captain reprimanded Greaves for his refusal to torture a prisoner, a fight ensued during which Greaves killed the captain and was immediately elected to replace him. Greaves earned a reputation as a humane and moral man despite being a pirate. He did not torture prisoners; he would not rob the poor and would not abuse or rape women. Greaves would simply steal and run. Having made off with a substantial sum of money, Greaves retired from piracy and became a plantation owner on the island of Nevis. Unfortunately, turning in pirates for bounty was extremely profitable, and when recognized by a former victim, Greaves was sentenced to hang. While he was in prison, a massive earthquake nearly destroyed the island, and Greaves was one of very few survivors. After being rescued by a whaling vessel, he became a pirate hunter and later received a pardon for his previous crimes. He’s one of the few pirates to die peacefully of old age.

Born to Scottish slaves on the island of Barbados, Greaves became a pirate when, in a desperate attempt to escape, he stowed away on a ship belonging to a notoriously cruel pirate named Captain Hawkins. Although forced to become a pirate, Greaves quickly adapted to the new role. However, life as a slave left him with little tolerance for brutality, and when the captain reprimanded Greaves for his refusal to torture a prisoner, a fight ensued during which Greaves killed the captain and was immediately elected to replace him.

Greaves earned a reputation as a humane and moral man despite being a pirate. He did not torture prisoners; he would not rob the poor and would not abuse or rape women. Greaves would simply steal and run.

Having made off with a substantial sum of money, Greaves retired from piracy and became a plantation owner on the island of Nevis. Unfortunately, turning in pirates for bounty was extremely profitable, and when recognized by a former victim, Greaves was sentenced to hang. While he was in prison, a massive earthquake nearly destroyed the island, and Greaves was one of very few survivors. After being rescued by a whaling vessel, he became a pirate hunter and later received a pardon for his previous crimes. He’s one of the few pirates to die peacefully of old age.

Henry Jennings began as a legitimate privateer operating from Jamaica but had a hard time changing his ways after the Treaty of Utrecht. In 1715, a Spanish fleet laden with exotic goods, silver and gold sank in a hurricane off the Florida coast. As pirates were not particularly adept at salvage operations, Jennings waited until the Spanish retrieved the treasure before seizing the staggering sum of gold. When the Governor of Jamaica refused to partake of Jennings’ windfall, instead vowing to hang the pirate, Jennings was forced to seek a friendlier port to call home. He and his crew made way for a small shantytown on the island of New Providence, now called Nassau. Though pirates had been using the harbor as a stopover, it wasn’t until Jennings arrived (becoming the unofficial mayor) that Nassau became the new Port Royal. During his presence in The Bahamas the waters teemed with pirates; so many that legitimate mariners avoided the area. In 1718, Woodes Rogers was appointed governor of The Bahamas and vowed to rid piracy from its waters. Rogers issued an ultimatum to all pirates: They could accept a King’s pardon and cease their acts of piracy or they would be hunted down and hanged. Having more money than he could ever spend, Jennings graciously accepted his pardon and lived out his life as a plantation owner. If you enjoy fictional pirates as well as real ones don’t miss our guide to islands featured in the Pirates of the Caribbean to visit on a luxury yacht.

Henry Jennings began as a legitimate privateer operating from Jamaica but had a hard time changing his ways after the Treaty of Utrecht. In 1715, a Spanish fleet laden with exotic goods, silver and gold sank in a hurricane off the Florida coast. As pirates were not particularly adept at salvage operations, Jennings waited until the Spanish retrieved the treasure before seizing the staggering sum of gold.

When the Governor of Jamaica refused to partake of Jennings’ windfall, instead vowing to hang the pirate, Jennings was forced to seek a friendlier port to call home. He and his crew made way for a small shantytown on the island of New Providence, now called Nassau. Though pirates had been using the harbor as a stopover, it wasn’t until Jennings arrived (becoming the unofficial mayor) that Nassau became the new Port Royal. During his presence in The Bahamas the waters teemed with pirates; so many that legitimate mariners avoided the area.

In 1718, Woodes Rogers was appointed governor of The Bahamas and vowed to rid piracy from its waters. Rogers issued an ultimatum to all pirates: They could accept a King’s pardon and cease their acts of piracy or they would be hunted down and hanged. Having more money than he could ever spend, Jennings graciously accepted his pardon and lived out his life as a plantation owner.

6 real pirates of the Caribbean

Jack Rackham, aka Calico Jack

Jack Rackham was not an especially ruthless pirate nor was he notably successful. What keeps Calico Jack in the forefront among his peers is that two of his crew — and likely the fiercest — were women. Rackham met Anne Bonny, the wife of a smuggler, in The Bahamas. The two fell in love, and when attempts to buy Bonny from her husband failed, Bonny joined Rackham’s crew as a pirate. Rackham and his crew soon captured a ship and gave that crew the option of joining him. Among the new additions was a magnificent swordsman. Over time, Bonny and this new crewman would forge a close relationship. When Rackham’s jealousy drove him into a rage, Bonny divulged that the new sailor was also a woman named Mary Read.

History has well documented that Rackham attacked several ships where Bonny and Read fought viciously and openly as women. The pair quickly became legendary throughout the Caribbean. As Rackham’s notoriety started to pale in comparison to his unusual crew, he began to succumb to alcohol. At the time of Rackham’s defeat, an already drunken crew (with the exception of Bonny and Read) panicked when the main mast was shot down. With defeat eminent, the crew dashed belowdecks to finish off the rum, knowing it would be the last they would ever have.

It is reported that Rackham was granted a last request to see Bonny before his execution. Still seething, she is quoted as saying, “I’m sorry to see you here, but had you fought like a man, you needn’t hang like a dog.”

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